TY - JOUR
T1 - Synthesis and crystal structures of N-Aryl-N-methylaminocyclohexanols
AU - Cresswell, Alexander J.
AU - Davies, Stephen G.
AU - Hewings, David S.
AU - Kurosawa, Wataru
AU - Lee, James A.
AU - Morris, Melloney J.
AU - Roberts, Paul M.
AU - Thompson, Amber L.
AU - Thomson, James E.
PY - 2013/12/31
Y1 - 2013/12/31
N2 - N-Aryl-N-methylaminocyclohexanols 10-12 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 10 crystallizes in the monoclinic space group Cc with cell parameters of a = 13.7366(2) Å, b = 13.7234(2) Å, c = 26.9057(5) Å, β = 93.0900(5), V = 5064.70(14) Å3 and Z = 16. Compound 11 crystallizes in the trigonal space group P 3 ̄ with cell parameters of a = b = 25.4429(4) Å, c = 9.6417(2) Å, V = 5405.27(16) Å3 and Z = 18. Compound 12 crystallizes in the monoclinic space group P21/n with cell parameters of a = 9.9511(2) Å, b = 11.5777(2) Å, c = 20.5968(4) Å, β = 95.5037(9), V = 2362.04(8) Å3 and Z = 8. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies revealed conformations of 10-12 which gave valuable information into the mechanism of the reaction during their formation. Graphical Abstract: Crystals of (RS,RS,RS)-3-[N-methyl-N-(4'-methoxyphenyl) amino]cyclohexane-1,2-diol, (RS,RS,RS)-3-(N-methyl-N-phenylamino)cyclohexane-1, 2-diol and (RS,RS,RS)-2-fluoro-6-(N-methyl-N-phenylamino)cyclohexan-1-ol were synthesised and their structures were studied by X-ray diffraction.[Figure not available: see fulltext.].
AB - N-Aryl-N-methylaminocyclohexanols 10-12 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 10 crystallizes in the monoclinic space group Cc with cell parameters of a = 13.7366(2) Å, b = 13.7234(2) Å, c = 26.9057(5) Å, β = 93.0900(5), V = 5064.70(14) Å3 and Z = 16. Compound 11 crystallizes in the trigonal space group P 3 ̄ with cell parameters of a = b = 25.4429(4) Å, c = 9.6417(2) Å, V = 5405.27(16) Å3 and Z = 18. Compound 12 crystallizes in the monoclinic space group P21/n with cell parameters of a = 9.9511(2) Å, b = 11.5777(2) Å, c = 20.5968(4) Å, β = 95.5037(9), V = 2362.04(8) Å3 and Z = 8. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies revealed conformations of 10-12 which gave valuable information into the mechanism of the reaction during their formation. Graphical Abstract: Crystals of (RS,RS,RS)-3-[N-methyl-N-(4'-methoxyphenyl) amino]cyclohexane-1,2-diol, (RS,RS,RS)-3-(N-methyl-N-phenylamino)cyclohexane-1, 2-diol and (RS,RS,RS)-2-fluoro-6-(N-methyl-N-phenylamino)cyclohexan-1-ol were synthesised and their structures were studied by X-ray diffraction.[Figure not available: see fulltext.].
KW - Amino alcohol
KW - Dihydroxylation
KW - Hydrogen bonding
KW - Hydroxyfluorination
KW - Olefinic oxidation
UR - http://www.scopus.com/inward/record.url?scp=84890453578&partnerID=8YFLogxK
UR - https://doi.org/10.1007/s10870-013-0460-8
U2 - 10.1007/s10870-013-0460-8
DO - 10.1007/s10870-013-0460-8
M3 - Article
AN - SCOPUS:84890453578
SN - 1074-1542
VL - 43
SP - 646
EP - 654
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 12
ER -